Two Roads Diverged (And I Took the One Less Travelled By)
by InkheartFirebringer
Summary: AU. The group was not alone on Blackwood Mountain that night. Or, eight times the Winchesters managed to help someone survive until dawn.


**Disclaimer: I don't own Until Dawn or Supernatural (or 'The Road Not Taken').**

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 **A/N: I've pretty much wanted to write an Until Dawn/Supernatural crossover from the minute my sister and I finished playing the game, but it's taken me ages to find a format I'm happy with. Finally nailed it this weekend after watching my sister play the game for the third time. Hopefully you enjoy it. :)**

 **P.S. Also, if anyone's confused, I wrote this as if each separate section was a different 'playthrough', where the named character was the only one to survive until dawn (with the help of the Winchesters, obviously.) That's why there are such obvious contradictions between each section regarding who lives and dies. :)**

 **P.P.S. I know the tags say Sam and Mike for the Until Dawn characters but that's only because there's a limit to how many people you can tag – I would have tagged 'em all if I could.**

 **P.P.P.S. This is season one Sam and Dean. :)**

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 **Two Roads Diverged (And I Took the One Less Travelled By)**

* * *

Two roads diverged in a yellow wood,

And sorry I could not travel both

And be one traveler, long I stood

And looked down one as far as I could

To where it bent in the undergrowth;

– The Road Not Taken,

Robert Frost

* * *

 **Ashley**

After the hunt was done, they found the distraught girl holed up in the basement of the big lodge. She was streaked with scarlet and she screamed bloody murder as they dragged her, kicking, out of the locked room.

" _No! No! It's not safe out there!"_

"It is now, sweetheart," Dean said through gritted teeth, ducking one of her wildly flailing hands.

"You don't understand," the girl sobbed, completely broken down. "They killed them all – tore – tore Chris' head off –" She broke off into agonised keening.

Sam and Dean exchanged grim looks over her head. Perhaps it wasn't a kindness that this girl had survived the night.

 **Mike**

" _Why?"_ Mike bellowed. His hands were trembling on the rifle but it was still fixed unerringly on the man standing across the derelict sanatorium from him. _"Why did you kill Jessica, you sick fuck?"_

The man gave a raspy laugh, even as the wolves on either side of him growled, a low menacing rumble that made the hairs rise on the back of Mike's neck. "I didn't kill anyone, boy. No one human at least." The goggles hiding his eyes shone eerily with reflected light.

"What the fuck does that mean?" Mike spat, finger tightening reflexively on the trigger. Then he froze as he felt something cold touch the back of his head and heard the distinctive sound of a gun cocking.

"It means you should take it down a notch," said a smooth voice from behind him.

The other man snorted and shook his head. "Took you long enough, Winchester."

"Gimme a break, old man, this isn't exactly an easy place to get to. Sammy, disarm this guy for me, would you?"

A third voice spoke, sounding exasperated. "Don't call me Sammy."

 _Shit, shit, shit!_ Mike's mouth was dry. Three-on-one odds were not good.

'Sammy' moved into his field of vision and to Mike's astonishment, the guy only looked a couple of years older than him, maybe twenty-two, twenty-three max. 'Sammy' gave him an encouraging smile, even as he took the gun from Mike's reluctant hands. "Don't worry. We've got everything under control."

"What the hell is going on?" Mike managed to say, bewildered and frightened and angry. _And hurting, oh God, Jessica, Jess, Jess –_

"Nothing that you'll believe. Not without seeing it for yourself, I'm betting," the man behind him said dryly. He felt the gun leave the back of his head. "What would you say if I told you a wendigo killed your girlfriend?"

Mike blinked as the man walked around into his field of vision. He looked about twenty-six or twenty-seven, handsome, well-built, with sharp green eyes. "I'd say you were full of it," Mike managed to say, vague recollections of the mythical monsters swimming up from his memory. But a sharp little doubt niggled as he remembered the hands that had pulled Jessica through the window, that strange silhouette he had seen through the scope of the sniper rifle.

"Thought as much," the man chuckled. "But you'll believe it when you see it. This night is far from over. Stick with us, kid, and you might just survive it."

 **Chris**

Chris cried out horror as the old guy's head was parted from his body, bright scarlet splattering across the pure white snow. He managed to bring the shotgun up and blast the wendigo away before it could turn and kill him too. The recoil sent the gun thudding back into his shoulder but he barely noticed the pain amidst the haze of fear and adrenaline.

He turned and ran, barely noticing where he was going. It was only important that it was _away from here._ A terrible, unearthly shriek came from behind him and he spun, bringing up the gun and firing again. The shot went wide and he had one moment of absolute horror and terror and _this is it, I'm going to die, oh God_ and _Ashley_ before two more gunshots rang out in the split second before the wendigo could land on him.

He watched, dumbfound, as it was thrown back away from him, and then a voice bellowed from the trees behind him, "Dude! Move your ass!"

Chris spun around to see a tall man with short brown hair holding a shotgun, next to an even taller man, with longer brown hair, also holding a shotgun. Tall Man winked at him and said "Come with us if you want to live."

Taller Man sighed exasperatedly. "Now is not the time, Dean."

Dean rolled his eyes. "There's always time for movie quotes, Sam."

Chris could only watch in disbelief, barely able to process the relative nonchalance of the two men. What was wrong with them? Why weren't they scared?

A bone-chilling shriek from somewhere off to his left immediately made him forget his momentary distraction and he bolted forward towards the two bickering crazies. At least _they_ were human.

 **Matt**

"Hey. Hey, dude. You okay?"

Matt shuddered and pressed himself closer to the cliff face, turning his face into the rock.

"I don't think he's okay, Dean."

"Yeah, I worked that out for myself, Sam."

A length of rope unfurled down the cliff and shortly after a pair of boots thudded into the rock next to Matt. A set of knees, clad in jeans, entered his range of vision. "Doesn't look very comfortable, sitting on this tiny shelf of rock."

Matt shook his head, not taking his eyes off the cliff wall.

"What's your name?" the voice persisted.

Several long seconds passed, then he rasped quietly, "Matt."

"Okay, Matt." The voice was gentle. "Why are you sitting here?"

This time the seconds stretched into minutes, ticking past agonisingly slowly. "She's dead."

"Who's dead?"

"Emily." Matt stared dully at the rock. "She just…fell. Slipped right over the edge right in front of me. I couldn't…couldn't catch her in time. The ledge wasn't safe, it was all iced over…but she insisted it was the fastest way out of the cable car station to the radio tower…we were going to call for help…"

"And then?" the voice prompted gently.

Matt blinked. "I tried to keep going. But there were a herd of deer…they were shoving and I couldn't get past and we were so close to the cliff…I panicked and hit them with the axe…"

There was a soft whistle beside him. "Ouch. They probably didn't like that."

"No." Matt's unfocused eyes gazed into the middle distance. "I was gonna climb back up. But…I think my leg's broken." He shifted slightly and his right leg came into view; white bone glinted in the red ruin of his calf.

The voice hissed in shock; a sharp, sympathetic inhale through clenched teeth. "Yeah, buddy. Looks pretty broken to me." It paused, hesitating. "If you give me a minute, I can rig up a harness. Don't worry, we'll get you out of here."

Matt shuddered. "I heard…I heard a terrible noise. Like…howling, but not like any howl I've ever heard before. I don't…I don't want go up there again. What if it's there?"

A hand clapped him on the shoulder. "Don't worry," the voice said bracingly. "We know what we're doing. We won't let it get you. You're in good hands."

Matt hesitated, then slowly nodded. "O-okay," he said haltingly.

"Good man," the voice said, with forced cheer. "Let's get to work."

 **Sam**

"I don't know who you are, or what you're doing here," Sam said evenly. "But you need to back off." She was aware of how insane she looked, skin streaked with dirt and soot and blood, the scent of petrol and smoke clinging to her clothes, with the old sanatorium burning behind her. She gripped the shotgun, holding it rock-steady, but her white knuckles gave away her tension.

"Whoa," said the taller man easily. His voice was friendly, soothing, but the shotgun in his own hands rather undermined the calming image he was going for. "It's okay, we're all friends here. You don't need that gun."

"I think I do actually." Sam's fingers tightened on the gun. It had been her constant companion and sole lifeline on this terrible night. "I'm not disarming until I get off this godforsaken mountain. Everyone…" Her even tone wavered for the first time. "Everyone else is dead. I'm not going to let those things kill me too."

Unbidden, her mind flashed back to mere minutes ago. _Mike running at her side, gun in hand, surrounding by cages and the frenzied howling of the wendigos, slashing claws through the bars. Then suddenly one was between them and Mike stumbled back, falling over a barrel of petrol, his shot going wide. She cried out in horror as its hand punched through his torso and a fountain of red burst out of his body. "Run, Sam!" he managed to choke and she heard the click as he flicked the lighter on. "Fuck you all," he snarled at the terrible creature and dropped the lighter into open barrel of fuel._

A yawning pit of black grief and rage opened up her chest and Sam breathed deeply, focusing on ignoring it. _Later. I can cry later._ Meanwhile, the two men were exchanging glances.

"What things?" the shorter-but-still-tall man asked, cocking his head to one side.

Sam inhaled evenly. Behind her, something went _whump_ as the flames found another canister of fuel and the new wave of heat washed over her. "You wouldn't believe me if I told you." She really wasn't in the mood to be called crazy after the night she'd had.

To her surprise, the taller man laughed a little. "Try us," he said dryly. "You might be surprised."

 **Josh**

Josh hummed and rocked back and forth on his stool a little. Mike had run out because he heard someone scream and he still hadn't come back yet. He sighed mournfully, slumping in his bonds. He really wish they'd let him have pizza. His shoulder was hurting quite a lot now, where Ashley had stabbed him with those scissors and the drying blood was itching and he couldn't scratch it –

Several more screams rang out in the distance, the sound of breaking glass and a dull _whump_. Orange light sprang up, flickering shadows stretching across the snow and Josh craned his head trying to see through the half-open doors. _Is that…is the lodge on fire?_ "Oh man, my parents are gonna _kill_ me," he moaned. "What the hell are you guys _doing_?"

Suddenly there was a loud thump on the roof above him, and the building shook. Josh looked up curiously. _What…?_

Two gunshots rang out, terrifyingly close and then even more terrifyingly, an awful, howling inhuman shriek that seemed to go on forever. There was a metallic clank, then a _sssssssssssskpt_ sound and brilliant light suddenly shone down through the cracks as another wave of brilliant orange fire swept over the roof, and the shriek abruptly cut off. "Got the sucker!" An unfamiliar male voice yelled triumphantly from outside.

"Calm down, Winchester, it's not over yet." The second voice was gruff and sounded older.

"What the hell is going on?!" Josh yelled, struggling to free himself from the rope. It looked like the roof might be on fire now and his dazed, circling thoughts had been snapped out of their repeating patterns by sudden sharp fear.

Silence fell outside, then the door creaked open. Framed by the darkness and swirling snow, stood an unfamiliar figure. He wore a green overcoat and a scarf covered his mouth. His eyes were hidden by goggles and he wore a set of metal canisters on his back, attached to something that vaguely resembled a power washer hose and gun.

Josh squinted. "Who are you?"

The stranger reached up and took off his goggles and pulled down the scarf, as he stepped in out of the snow, and Josh's eyes widened. "Hey, you're that guy that kept telling my parents to get off the mountain!"

The stranger snorted. "Too bad they didn't listen, or your friends might not have had to die like that. What're you doing in here anyway, kid?" he added, looking at Josh's bound hands.

 _What…? Dead?_ Josh's mind ground to a halt. _Mike said I killed Jess…but I didn't! I would remember that! …Wouldn't I? I would. They can't be dead…_

"Kid?" the man prompted.

Josh raised dazed eyes to meet his and replied distractedly, "They…they didn't like my joke."

 **Emily**

"Sweetheart, we haven't got all day here," the voice drifted up to Emily and she ground her teeth and wedged herself further back in the little crevice she had found in the wall of the mine tunnel. To her annoyance, her hands shook on her improvised weapons and she forced them to still. Emily had never been one to give up or admit defeat, but some part of her mind whispered that this wasn't looking good. She was one girl, with a homemade torch and a single flare gun, against three men armed with shotguns and flamethrowers.

"Fuck you guys," she spat furiously, burying her fear away deep inside her. She couldn't afford to be afraid right now. "You're fucking crazy if you think I'm going anywhere with you, after you killed Josh and Matt and sabotaged the cable car station. Is this fun for you, huh? Trapping us on this fucking mountain and killing and torturing us, is this your idea of a fun weekend? Because newsflash you bastards, I'm not going to just lie down and die! If you want to kill me, you'll have climb up here and pry me out, and _you can be fucking sure I won't make it easy_!"

The echoes of her shout died away and there was a quiet whistle from below. "Jeez, sweetheart. You've got some balls." The guy sounded impressed. "But you've got the wrong end of the stick. We're not here to hurt you, we're here to help."

Emily couldn't help her snort of disbelief.

"Yeah, I guess I wouldn't believe us either," he said dryly. "I'd rather not do story time down here, but you're not leaving us much choice. Sam, would mind keeping watch?" he spoke to one of the other men. "Don't want something to sneak up on us."

There was a sigh and the sound of someone moving off. Emily gripped her makeshift weapons tighter. _Two instead of three. That's… marginally better odds. Still not great,_ she acknowledged grimly.

"Sweetheart?" his voice cut into her thoughts and she nearly snarled at the pet name. Still, she wasn't giving him her real name. "Just hear us out. You see, this all started in 1952…"

 **Jessica**

Jess shivered as she limped along the tunnel. She had at least managed to find a coat, but it was stiff with age and dirt, and freezing cold besides. A little voice in the back of her mind was whispering that it was likely she would die of hypothermia or exposure long before she found her way out of these mines. Or before the monster found her first.

A full-body shudder overtook her at that thought, a wave of goosebumps travelling over her and making all her hair stand on end in terror. She shoved the thought away. _Don't think about it. Don't think about it._

Jess gritted her teeth as a loose rock made her stumble and jarred her leg, sending a bolt of pain through her. There didn't seem to be a single part of her that _didn't_ hurt at the moment and she was pretty sure that she had at least a few broken ribs.

A sudden noise up ahead made her freeze. Trying to ignore the feeling of overwhelming terror, Jess stepped back carefully, groping for the handle of the shovel she had seen propped up against the wall. Her abused body cried out at carrying the extra weight of the tool but she ignored the throbbing pain, hefting the shovel as much as she dared. If she was going to die, it would be with a weapon in her hands.

Creeping forward, Jess peered around the bend in the tunnel. A huge shadow loomed up in front of her, backlit by orange light, and she shrieked, swinging the shovel as hard as she could. A big hand snapped out and caught the tool, arresting its movement; Jess didn't hesitate, curling her right hand into a fist and throwing the best punch she could, despite her injured state.

"Whoa!" a deep voice cried, as the figure leaned back to avoid the punch and grabbing her hand. "Slow down! I'm not trying to hurt you."

But Jess had already all but melted with relief. The voice and the hand restraining hers, while unfamiliar, were undoubtedly human. "Sorry – I – I thought –" she choked.

"Hey," the voice softened. "It's okay. C'mere –"

Jess found herself towed gently forward, out of the tunnel into a wider cave. An old-fashioned oil lantern sat on top of crate and she nearly burst into tears at the sight of its welcome golden light. She looked up into the unfamiliar face of a tall young man, maybe three or four years older than her, with shaggy brown hair. Despite his height and the broadness of his shoulders, there was something undeniably gentle about him.

"Sorry," she repeated, still shaking. "I thought you were a monster." Instantly she winced, knowing how crazy it sounded.

But the young man's gaze sharpened. "You've seen it?" he asked urgently.

Jess's eyes widened. "You mean you have too?" Relief filled her, that she wouldn't have to convince him to both believe her and of the urgency of the need to get out of there.

He shook his head. "No. But it's why I'm here." He gestured behind him, and Jess's gaze fell on a shotgun, gleaming in the lantern light, and another strange weapon she couldn't identify.

"You're hunting it?" Jess asked in disbelief.

He shrugged. "It's what we do, me and my brother. I'm Sam, by the way," he said, holding out his hand and smiling a little.

She smiled back. "I'm Jess," she said, shaking his hand. His eyes widened at her statement and she thought he might have paled a little, although it was hard to tell in this light.

"Hi…Jess. Nice to meet you." He sounded a little choked, but managed to maintain his smile. "Don't worry. I'm going to get you out of here."

* * *

 _ **Omake**_

Blackwood Mountain."

A file slapped down on the table in front of Dean and he looked up in surprise, burger hanging out of his mouth.

"A hunt, Dean." Sam pulled out a chair, dropping into it. "Dude, that's gross," he added, looking at the burger.

His brother crammed in the rest of the beef manfully and spoke deliberately through a mouthful half-chewed food. "What kinsh ofsh unt Sshammy?"

"Annnd, that's worse," Sam said, grimacing at the sight of the masticated burger as Dean talked. "Also, don't call me Sammy."

"Sure, thing Sammy," Dean said amicably, after swallowing what looked like an entire pound of cooked meat. "Now, what's the hunt?"

Sam glared, then with some effort shook off his disgust in favour of professionalism. "Right, well…" he opened the file. "Blackwood Mountain, located in the Rockies, Alberta –"

"Canada?"

"No, Dean, Alberta, Japan. Of course it's Alberta, Canada."

"Someone's PMSing. Calm down, Samantha."

" _The hunt_ ," Sam stressed the words, "Is on Blackwood Mountain, which is the site of several 'mysterious' occurrences. Or suspicious ones. In 1952, there was some sort of mine collapse due to poor maintenance and a group of miners were trapped underground for nearly a month. Only twelve made it out alive and were admitted to the Blackwood Pines Sanatorium for treatment for post-traumatic stress. That's where records get hazy but the sanatorium closed soon afterwards and was never re-opened." He paused and flipped over a page. "Then, just last year, a pair of girls went missing on the mountain in a snowstorm – it says that Hannah and Beth Washington left their family lodge, where they were staying with a group of friends and never returned. The police couldn't find any trace of them."

"Let me guess," Dean said, sitting back in his chair. "The lodge is right near the old sanatorium and mines?"

"Bingo." Sam looked grim. "I'm thinking maybe vengeful spirits?"

"Could be, could be." Dean chewed his straw thoughtfully. "Either way, looks we've got a hunt on our hands." He stood and shrugged on his jacket, clapping his brother on the shoulder as he passed. "Let's get this show on the road, Sammy."

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 **A/N: So yeah, that little extra scene was left over from when I trying to find the right format to write this story in, but I still liked it enough that I wanted to share it. It's more of a prologue than anything, but it kinda ruined the flow to put it at the start, so I stuck it in as an extra scene. :)**

 **Regardless, I hope you enjoyed reading this and please leave a review, if that is the case. :) I'm currently working on another Until Dawn story (not a Supernatural crossover this time) and any fuel for writing is welcome.**

 **P.S. I highly recommend the live action trailer for Until Dawn if you've not seen it yet. It's on YouTube, it's 2 minutes and 16 seconds long and it's called 'Until Dawn - The Road Not Taken Trailer | PS4'. The poem that's being read over the trailer is the full version of the poem quoted at the start of this story. :)**


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